Dimethyl Sulfoxide → 2-Acetyl-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]-ethyl}-6-heptenamide

HRID 890712노트

반응식

HRID 890712 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:38]=[CH:39][C:40]=1[O:41][CH3:42])[CH2:16][C:17]1[NH:22][C:21](=[O:23])[C:20]([CH:24]([NH:26][C:27](=[O:37])[CH:28]([CH:34]([OH:36])[CH3:35])[CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[CH3:25])=[N:19][N:18]=1.C(N(CC)CC)C>ClCCl>[C:34]([CH:28]([CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33])[C:27]([NH:26][CH:24]([C:20]1[C:21](=[O:23])[NH:22][C:17]([CH2:16][C:15]2[CH:38]=[CH:39][C:40]([O:41][CH3:42])=[C:13]([O:12][CH3:11])[CH:14]=2)=[N:18][N:19]=1)[CH3:25])=[O:37])(=[O:36])[CH3:35]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 135697922N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-2-(1-hydroxyethyl)-6-heptenamide

생성물 1

HCID 1356979142-Acetyl-N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]-ethyl}-6-heptenamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-70 °C

실험 절차

100 mg (0.76 mmol) of oxalyl chloride in 5 ml of dichloromethane are treated dropwise at −70° C. with 130 mg (1.64 mmol) of dimethyl sulphoxide. The mixture is stirred at −70° C. for 30 min, then 280 mg (0.63 mmol) of N-{1-[3-(3,4-dimethoxybenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-2-(1-hydroxyethyl)-6-heptenamide (Example 29A) are added. After a further 30 min, during which the temperature in the batch rises to about −60° C., 320 mg (3.15 mmol) of triethylamine are added and the cooling bath is then removed. If the batch temperature is warmed almost to room temperature, 10 ml of water are added and the phases are separated after stirring briefly. The dried organic phase is chromatographed in dichloromethane/methanol 50/1.

후처리

  1. waitAfter a further 30 min
  2. customrises to about −60° C.
  3. customthe cooling bath is then removed
  4. temperatureIf the batch temperature is warmed almost to room temperature
  5. addition10 ml of water are added
  6. customthe phases are separated
  7. stirringafter stirring briefly
  8. customThe dried organic phase is chromatographed in dichloromethane/methanol 50/1

출처 및 근거

ORD 기록
ord-b067f4a5823f41d1b226fdbd570f6f94
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06998402B2

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